The Risk of Asking a Question

Growing up, I was told—like most of you, I’d guess—that there was “no such thing as a stupid question.”

Parents, teachers, coaches all encouraged me to ask what was on my mind, whatever it happened to be. The implication was that any question would be OK to ask.

But that wasn’t exactly true. Because while it might be true that there were no stupid questions, there were risky questions—questions that could potential impose a high cost for the asker.

Even as a child, we all had an intuitive sense that there was more to questions than just whether they were stupid or not. It’s why we hesitated, and why we needed to be encouraged to ask what was on our mind.

And our intuition was right—there is more to asking a question. Unfortunately, the overly simplistic view that what holds us back is the fear of asking a “stupid” question keeps us blind to what that is.

When we think about questions less in terms of stupid/smart—or even good/bad—and more in terms of risk/reward, the challenge with asking what’s on our mind becomes easier to see. There are at least four risk/reward calculations to asking a question as far as I can tell, including:

  1. The risk of revealing you don’t know something versus the reward of getting the information now;

  2. The risk of revealing you didn’t understand something versus the reward of learning it now;

  3. The risk of revealing you didn’t hear something and making people hear it again versus the reward of you hearing it once;

  4. The risk of being willing to reveal anything at all… versus the reward of being willing to reveal anything at all.

The risk of revealing you didn’t know something

Who amongst us hasn’t been in a meeting when, upon hearing something, we thought to ourselves, Was I supposed to know that? The “that” in question might be small, like the date of the next meeting, or big, like that position you were hoping to get promoted into got filled with an outside candidate.

But what’s stress inducing usually isn’t the information that wasn’t known, it’s the recognition that information was flowing around you without flowing to you. And the risk of asking about it could be that you not only confirm your fears that you’re not in the loop, but that you put that fact on public display.

Of course, the risk may also be negligible—perhaps there was an email you missed—which is what makes it risky and not costly. We can’t be sure exactly what the consequence will be. Still, until the adrenaline stops flowing and you can start thinking clearly again, it’ll be very hard to relax.

The risk of revealing you didn’t Understand something

In the best-case scenario, the risk of revealing that you don’t understand something is that you signal that you need a little help, maybe in the moment, or maybe after the fact, from a book, class, or other resource. In the worst-case scenario, however, you risk signaling that you don’t have the skills required to do your job, or—less extreme and far more likely—that you don’t have the skills required for the next job up that you want, which probably doesn’t put your job in jeopardy but does slow your career trajectory.

The risk of revealing you didn’t hear something

Writing this brings back memories of being called on in English class when my teacher knew I hadn’t been paying attention. My attempt to jump into the conversation was so off base that he worked what I said into our next test. It was funny, I deserved it, and it ended up being a great learning moment.

But as an adult, the risk of being perceived as not paying attention—especially repeatedly—rarely ends so lightly. Especially if the person being ignored is (a) in a position of authority, and (b) has thin skin.

The risk of being willing to reveal anything at all

This is the risk with high potential rewards but also high potential costs. It’s also less obvious than the first three. So rather than explain this risk, let’s illustrate it with an example:

Consider a meeting about a project you’re in charge of. Imagine a VP—the head of your division—at the head of the table. On either side or her, imagine another division head. In fact, fill the room with a total of 6 VPs (including your division head), add yourself, and sitting directly across from you, imagine a Business Analyst. Eight people, gathered for an update on your project.

Now imagine the business analyst sharing a performance baseline he’s completed. And while he’s talking, he states, quite unexpectedly, that the expected ROI of your project will be $1.5 million less than you had estimated in your original plan.

You sit, surprised, and ask yourself, Do I ask the business analyst about the discrepency?

The potential reward of asking your question comes from demonstrating thoroughness, integrity, and trustworthiness to the VPs in the room, and from engaging the analyst directly in problem solving. That’s clear. But what about the risk?

Assume that you can frame your question perfectly—direct yet polite, curious without being challenging or defensive—and there’s no concern about offending anyone. Truly, you’ll get an A+ for your semantics, so we don’t have to worry about any interpersonal risks. (Good job, by the way.)

You still have potential problems:

First of all, there is the problem of not knowing this critical information. Your question will reveal a process breakdown, making all the VPs wonder why you and the analyst didn’t coordinate on something so fundamental before the meeting. Will they blame SNAFU on you? The analyst? Both of you? Or will they blame one of your bosses? And are you prepared for the consequences of this reveal? After all, you were just surprised by the information that the analyst shared… is there another surprise awaiting you?

Secondly, your question may also reveal a lack of understanding: Either you or the business analyst is on course to make a $1.5 million mistake. Assuming that you’re an expert in your domain, and the analyst is an expert analyst, your question will reveal either that the business analyst came up with the wrong number because he didn’t know something about your business, or that you came up with the wrong number because you didn’t understand something about how to calculate an ROI. So even if the division head ignores the process breakdown, you’re still at risk of revealing that you just put an ROI calculation in front of an executive without first making sure you understood what you were doing.

Third, there is some risk of revealing you didn’t hear something. Maybe the analyst’s number had been shared in a previous conference call, and you missed it because you were multitasking? Maybe you just didn’t hear him right a moment ago? Anything’s possible. In the scheme of things, probably the smallest risk in the list.

Which brings us to the biggest risk: revealing your willingness to reveal anything at all. Or, to put it another way, revealing the courage to ask the question in spite of the risks.

Asking this question signals to everyone in the room your willingness to call out a mistake in front of powerful people. Maybe the goof is on you, maybe it’s on the analyst, maybe the whole thing is a big test designed to see how you’ll react… but whatever the reason you find yourself here, the one thing everyone understands is that your question carries real risk, and so asking it will signal to everyone that if you’re in a room when something weird goes down, you will ask the hard question.

This should make you a hero. It’s what everyone wants! And if you work in an organization that rewards this behavior, good for you, protect that culture! But too often, this reveal creates a huge problem. Because while the highest ranking person in the room (in this case, your division head) is likely to appreciate your guts, everyone else has just been put on notice to be careful around you, because you will out them. And I did say “likely”—courage is never guaranteed to win you friends.

As ironic as it is, unless it’s actively supported from the top, courage typically doesn’t beget courage in others as much as it begets cowardice. I’d write more about this but it hurts my soul to even think about.

And yes, there is risk in not asking your question, too. But as the default course of action is to continue to keep sitting in your chair, not asking anything, your brain doesn’t have to spin on the decision to continue to do that. It only needs to determine if changing course is worth it.

Risks and rewards.

All of which is to say, if you want to get people in your organization speaking up more, maybe consider looking at the risks your people bear, rather than the rewards they can expect, to unlock the behavior you’re looking for.

Jason Seiden